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125318

Sigma-Aldrich

Citraconic anhydride

98%

Sinónimos:

2-Methylmaleic anhydride, 3-Methyl-2,5-furandione, Citraconic acid anhydride, Methylmaleic anhydride, Monomethylmaleic anhydride

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About This Item

Fórmula empírica (notación de Hill):
C5H4O3
Número de CAS:
616-02-4
Peso molecular:
112.08
Beilstein:
1835
Número CE:
210-459-0
Número MDL:
MFCD00005522
Código UNSPSC:
12162002
ID de la sustancia en PubChem:
24847660
NACRES:
NA.23
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densidad de vapor

4 (vs air)

Ensayo

98%

Formulario

liquid

índice de refracción

n20/D 1.471 (lit.)

bp

213-214 °C (lit.)

mp

6-10 °C (lit.)

densidad

1.247 g/mL at 25 °C (lit.)

cadena SMILES

CC1=CC(=O)OC1=O

InChI

1S/C5H4O3/c1-3-2-4(6)8-5(3)7/h2H,1H3

Clave InChI

AYKYXWQEBUNJCN-UHFFFAOYSA-N

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Descripción general

Citraconic anhydride is a derivative of maleic anhydride and is also known as 2-methylmaleic anhydride. It is highly reactive due to the presence of anhydride groups and can undergo hydrolysis, esterification, amidation, and addition reactions. It can be used as a crosslinking agent to create covalent bonds between polymer chains, enhancing the mechanical strength and thermal stability of the polymer network. They arepotential tools for bioconjugation and immobilization of bioactive molecules.

Aplicación

Citraconic anhydride can be used:

  • As an electrolyte additive for high-temperature pouch lithium-ion batteries. Citraconic anhydride reduces the interfacial impedance of pouch cells during high-temperature storage and enhances their stability.[1]
  • As a pH-sensitive linker to surface functionalization of biomolecules used in drug delivery systems. The high pH sensitivity of citraconic anhydride conjugates is attributed to the presence of a double bond that restricts the separation between the amide and carboxylic acid groups.[2]
  • As a reagent to synthesize new thiopyrano[2,3-d][1,3]thiazole derivatives via hetero-Diels–Alder reactions. These thiopyrano derivatives exhibit diverse biological activities such as anticancer, antiviral, and antitrypanosomal.[3]
  • As a co-monomer in the ring-opening polymerization with d-xylose 3,5-anhydrosugar derivative to form novel sugar-derived polyesters, with up to 100% renewable content. This can serve as a sustainable feedstock for polymer synthesis.[4]

Pictogramas

Health hazardCorrosion
GHS08,GHS05

Palabra de señalización

Danger

Frases de peligro

H314,H317,H334

Clasificaciones de peligro

Eye Dam. 1 - Resp. Sens. 1 - Skin Corr. 1B - Skin Sens. 1

Código de clase de almacenamiento

8A - Combustible corrosive hazardous materials

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

231.8 °F - closed cup

Punto de inflamabilidad (°C)

111 °C - closed cup

Equipo de protección personal

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificados de análisis (COA)

Lot/Batch Number
STBK6794
STBK6248
STBK6247
STBK3369
STBK4794

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Anh H Cao-Pham et al.
Journal of comparative physiology. B, Biochemical, systemic, and environmental physiology, 189(6), 693-706 (2019-10-06)
In light, giant clams can increase rates of shell formation and growth due to their symbiotic relationship with phototrophic zooxanthellae residing extracellularly in a tubular system. Light-enhanced shell formation necessitates increase in the uptake of Ca2+ from the ambient seawater
Citraconic anhydride as an electrolyte additive to improve the high temperature performance of LiNi0?6Co0?2Mn0?2O2/graphite pouch batteries
Chengyun Wang, et al.
Journal of alloys and compounds, 805, 757-766 (2019)
A Fischer et al.
Biomedica biochimica acta, 50(10-11), S169-S174 (1991-01-01)
Several amino acid derivatives with the negatively charged N alpha-protecting groups Maleyl (Mal) and Citraconyl (Cit) were synthesized and used in enzyme-catalyzed peptide synthesis. Compared to commonly used alpha-amino protecting groups in chemical peptide synthesis (Z, Fmoc, Boc, etc.), these
Synthetic Communications, 23, 1321-1321 (1993)
Macromolecules, 25, 102-102 (1992)
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Questions

1–2 of 2 Questions  

  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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